Jump to content

Main menu Navigation ●Main page ●Contents ●Current events ●Random article ●About Wikipedia ●Contact us ●Donate Contribute ●Help ●Learn to edit ●Community portal ●Recent changes ●Upload file

●Create account ●Log in ●Create account ● Log in Pages for logged out editors learn more ●Contributions ●Talk

(Top) 1 Production 2 Safety 3 References

4-Vinylcyclohexene

●تۆرکجه ●Čeština ●Deutsch ●Esperanto ●فارسی ●Nederlands ●Српски / srpski ●Srpskohrvatski / српскохрватски ●Suomi ●தமிழ் ●中文 Edit links ●Article ●Talk ●Read ●Edit ●View history Tools Actions ●Read ●Edit ●View history General ●What links here ●Related changes ●Upload file ●Special pages ●Permanent link ●Page information ●Cite this page ●Get shortened URL ●Download QR code ●Wikidata item Print/export ●Download as PDF ●Printable version In other projects ●Wikimedia Commons Appearance From Wikipedia, the free encyclopedia

4-Vinylcyclohexene
Names

Preferred IUPAC name 4-Ethenylcyclohex-1-ene
Other names Butadiene dimer 4-Ethenylcyclohexene 1-Vinyl-3-cyclohexene 4-Vinyl-1-cyclohexene
Identifiers
CAS Number	100-40-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82377
ChEMBL	ChEMBL1330194
ChemSpider	7218^Y
ECHA InfoCard	100.002.590
EC Number	202-848-9
KEGG	C19310^Y
PubChem CID	7499
RTECS number	GW6650000
UNII	212JQJ15PS^N
CompTox Dashboard (EPA)	DTXSID3021437
InChI InChI=1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2^Y Key: BBDKZWKEPDTENS-UHFFFAOYSA-N^Y InChI=1/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 Key: BBDKZWKEPDTENS-UHFFFAOYAZ
SMILES C=CC1C\C=C/CC1
Properties
Chemical formula	C₈H₁₂
Molar mass	108.184 g·mol⁻¹
Appearance	Colorless liquid
Density	0.8299 g/cm³ at 20°C
Melting point	−108.9 °C (−164.0 °F; 164.2 K)
Boiling point	128.9 °C (264.0 °F; 402.0 K)
Solubility in water	0.05 g/L^[1]
Solubility	soluble in benzene, diethyl ether, petroleum ether
Vapor pressure	2kPa
Refractive index (n_D)	1.4639 (20 °C)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H351
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)	0 3
Flash point	21.2 °C (70.2 °F; 294.3 K)^[3]
Autoignition temperature	269 °C (516 °F; 542 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	2563 mg/kg (oral, rat)^[2]
Safety data sheet (SDS)	Oxford University
Related compounds
Related compounds	Buta-1,3-diene Cyclohexene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

4-Vinylcyclohexene is an organic compound consisting of a vinyl group attached to the 4-position of the cyclohexene ring. It is a colorless liquid. Although chiral, it is used mainly as the racemate. It is a precursor to vinylcyclohexene dioxide.^[4]

Production[edit]

It is produced by buta-1,3-diene dimerization in a Diels-Alder reaction.^[5]^[4] The reaction is conducted at 110 - 425 °C at pressures of 1.3 - 100 MPa in the presence of a catalyst. A mixture of silicon carbide and salts of copperorchromium comprises the catalyst. A competing product is 1,5-cyclooctadiene.

Safety[edit]

4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC ("possibly carcinogenic to humans").^[3]

References[edit]

^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 8–111. ISBN 0-8493-0594-2.

^ "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. Archived from the original on 2010-12-31. Retrieved 2009-04-19.

^ ^a ^b "4-Vinylcyclohexene" (PDF). IARC. Retrieved 2009-04-19.

^ ^a ^b Schiffer, Thomas; Oenbrink, Georg. "Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_205.pub2. ISBN 978-3527306732.

^ Wittcoff, Harold; Reuben, B. G.; Plotkin, Jeffrey S. (1998). Industrial Organic Chemicals (2 ed.). Wiley-Interscience. pp. 236–7. ISBN 978-0-471-44385-8. Retrieved 2009-04-19.

Retrieved from "https://en.wikipedia.org/w/index.php?title=4-Vinylcyclohexene&oldid=1195583015" Categories: ●Cyclohexenes ●IARC Group 2B carcinogens ●Vinyl compounds Hidden categories: ●ECHA InfoCard ID from Wikidata ●Articles with changed FDA identifier ●Chembox having GHS data ●Articles containing unverified chemical infoboxes ●Chembox image size set ●Articles with short description ●Short description is different from Wikidata ●This page was last edited on 14 January 2024, at 12:47 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view